Kevin wakes up on Garth's boat and marks off another day. After pouring himself a cup of coffee, he goes to work translating the tablet. Days pass until Kevin finally finishes the translation. His nose starts bleeding and he collapses.
At the Letters base, Dean sets up his own room and puts a photo of himself and Mary on the desk. Sam comes in and Dean talks about he finally has a room of his own with no smell. He goes to get himself some food and Sam notices the photo of Mary and smiles. Later, Sam is going over the Letters' books when Dean brings in some food that he made and explains that he's nesting. Kevin calls on Dean's phone and tells him to come quick and then cuts out.
The Winchesters drive to the boat and find Kevin throwing up in the bathroom. He admits that he hasn't been sleeping well and may have had a stroke, but it's worth it because he figured out how to close the gates of Hell. Kevin has found a spell that has to be recited after completing three trials that God built. He's only translated one trial which involves killing a hellhound and bathe in its blood. Dean goes off to get Kevin some food while Sam starts looking for someone who could have made a crossroads deal. As he works, Sam tells Kevin that he needs to relax. However, Kevin says that he wants to seal the gates because he can't go out until he does. Sam understands but tells him that saving the world is a marathon, not a sprint.
Dean returns with food and Sam has confirmed that ten years ago there were demon signs in Shoshone, Idaho. The Cassitys, small-time farmers, struck oil on their land in 2003. The Winchesters take off after Dean gives Kevin aspirin and pep pills, saying it's time to work through the pain.
The brothers arrive at the Cassity ranch. They run into the manager, Ellie, and pass themselves off as drifters looking for work. Carl Granville, who is married to Alice Cassity, comes over and introduces himself. He figures the Winchesters are swell and tells Ellie to hire them. She takes them to the bunkhouse and warns them that it's crap work. The Winchesters are soon mucking out the stables and hear Ellie arguing with Alice, who tells the manager to do things her way. Once she leaves, Ellie comes over and admits that there's not much she can do when Alice is the boss. Dean suggests that they get a drink but Ellie just walks off. The brothers figure that Alice is the one who made the deal and decide to stake her out.
That night, Carl and Alice are having dinner when they hear a howling in the distance. It spooks the houses and Alice goes to check on them. Dean and Sam follow her to the stables... while a hellhound attacks Carl, ripping his throat out.
Once the murder is reported, the sheriff comes out. He wonders who the Winchesters are and Ellie says that their new workers. He suggests that it was a wolf but Ellie doesn't believe it and goes to call the family. Once she leaves, the sheriff says that having all of the Cassitys under one roof could be tough. Once they're alone, Dean figures that the hellhound has claimed its victim and moved on. As he goes to pack, Sam goes to the stables. He finds Alice looking after a horse and asks if she's okay. She says that she is and is surprised because she thought she loved Carl, but can't remember why. Alice talks about how she went to school with Carl and they got together ten years ago when she fell in love with him for the first time.
When Sam goes to the bunkhouse, Dean suggests that they summon a hellhound. Sam warns that Crowley would send dozens of hellhounds after them, and tells him what he learned about Alice. They figure that the crossroads demon signed multiple deals and suggests that they stay and scope them out. Dean gives Sam two days to get results before they do it his way.
The next day, Noah Cassity is the first to arrive. Ellie tells the Winchesters that he's 71 and has married five times. His newest wife is Ivanka, a lingerie model. His middle daughter is Cindy, is a top country singer. The youngest is Margot, who ran away to live in Paris just before Carl and Alice married. Ellie tells the Winchesters that she'll need one of them inside pouring drinks and the other one manning the grill. Dean takes charge of the grill while Sam pours drinks. Margot expresses her condolences to Alice, who doesn't feel anything. Cindy insults everyone and then tells Alice that Margot and Carl were together before Carl ended up with Alice. Sam talks to Ellie in the kitchen and wonders how she puts up with the family, and she says that she devotes herself to the ranch and tunes them out.
The family enjoys their dinner and remembers the last time they had a meal together. It was when a traveling salesman visited them, and they finally remember his name was Crowley. Sam overhears them and tells Dean and they figure he's sending the hellhound to collect. Kevin calls to tell the brothers that he found something on the tablet saying that they can be seen through glass covered with burning holy oil. Sam goes back inside to watch the family while Dean goes to get some holy oil from the Impala.
Once Sam goes back inside, he sees Margot and Noah going outside to hunt down the wolf. Sam goes after them and offers to go with them, and Margot reluctantly gives him a shotgun.
Dean puts on an old pair of glasses and lights the holy oil. He scans the area and sees Ellie coming, and quickly puts out the fire. She invites Dean to come to her room and have sex, and admits that she doesn't usually do it. Dean says that he can't and Ellie steps back, embarrassed. He tells her that he wants to and asks for a rain check, but she tells him that it's one night only and walks away.
Sam, Noah, and Margot go into the woods, unaware that a hellhound is stalking them. When he hears something behind them, Sam moves off on his own and Noah circles behind him and gets the drop on him. They realize that Margie is missing just as they hear her scream. They follow the sound and find a hellhound tearing her apart. Sam shoots, driving it off, and gets Noah back to the house.
Once the family is gathered, Dean tells them that a hellhound is after them because Crowley sent it. Dean asks them to admit which ones sold their souls. When no one says anything, Sam goes to seal the house while Dean tells everyone to sit down and shut up. He then hands out handcuffs and fastens everyone to the furniture. Sam explains that they may start seeing and hearing things so the handcuffs are for their protection. Dean tells Sam to stay in the house while he goes after the hellhound. Sam protests and Dean points out that in the past, one of them has had to die. He says that he's a grunt and Sam is the brains, and admits that he doesn't see a way out at the end. All Dean wants is for Sam to get out and have a life, so he'll do the trials alone and will shoot Sam in the leg if he tries to follow him. Dean then goes out to patrol the grounds and hears music coming from the barn.
Cindy and Noah exchange accusations when Sam comes back. He points out that they struck oil when there wasn't any and Alice remembers that Margie was the one who wanted them to have money so they'd be happy.
Dean finds Ellie dancing in her room to the music. She says that he's just in time and kisses him, but Dean tells her to stay in her room with the door locked. He explains about the hellhound and she says that she knows... because it's coming for her.
Noah says that he has to use the bathroom and Sam tells him to hold it. Sam looks out the window and sees the hellhound prowling the grounds. Meanwhile, Alice manages to slip out of the handcuffs and runs outside to her car. Sam goes after her and drags her back to the house, and sees the hellhound approaching. He sends her to the house and tries to spot the creature.
Ellie explains that her mother took a job there and she grew up there. She met Crowley after the dinner when she saw him kissing Margie. Crowley found Ellie and granted her wish to cure her mother of Parkinson's. Dean says it was a stupid move but Ellie says that she would do anything for her mother and asks what Dean would do for his mother. Ellie admits that Crowley didn't explain about the ten-year limit and Dean realizes that the demon didn't warn Carl or Margie either. She learned from Carl about his deal when he was drunk, and decided not to run. They hear howling in the distance and Ellie sees Dean's face transform. He tells her that it's a hallucination brought on by the hellhound's presence, makes a circle of goofer dust, and tells her to stay inside no matter what.
Dean steps out into the stable and puts on the glasses. He sees the hellhound, which ducks into the shadows and then lunges at him, knocking off the glasses. When it comes at Dean again, Sam arrives and shoots it. The hellhound lunges at him and he cuts its throat, bathing in its blood.
Once Dean and Sam wrap up their wounds, the brothers tell Ellie that they'll make her a hex bag so Crowley can't find her, and then she'll go on the run. Dean asks for a moment and then tells Sam that they can save Ellie from going to Hell if they seal it. He takes the spell and reads it, but nothing happens. When Dean says that he'll track down another hellhound, Sam says that he's going to finish the last two tests and seal Hell's gate. Sam says that he wants to live and if Dean comes with him, he'll take him to the end. He assures Dean that he's more than just a grunt and asks Dean to believe in him. Dean considers and then hands him the spell back. Sam recites the words and then collapses in agony as a burst of red-hot energy spreads up his right arm. He turns and tells Dean that he can do it.